CN114644897A - Ultrathin conductive adhesive film and preparation method thereof - Google Patents
Ultrathin conductive adhesive film and preparation method thereof Download PDFInfo
- Publication number
- CN114644897A CN114644897A CN202210261080.0A CN202210261080A CN114644897A CN 114644897 A CN114644897 A CN 114644897A CN 202210261080 A CN202210261080 A CN 202210261080A CN 114644897 A CN114644897 A CN 114644897A
- Authority
- CN
- China
- Prior art keywords
- parts
- conductive adhesive
- adhesive film
- ultrathin
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002313 adhesive film Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 239000004814 polyurethane Substances 0.000 claims abstract description 43
- 229920002635 polyurethane Polymers 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- ZKVGXVGEPRBBQV-UHFFFAOYSA-N CN1C(NC(N(C1=O)CC=C)=O)=O.C1CO1 Chemical compound CN1C(NC(N(C1=O)CC=C)=O)=O.C1CO1 ZKVGXVGEPRBBQV-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 29
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 25
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 239000012948 isocyanate Substances 0.000 claims abstract description 24
- 239000011231 conductive filler Substances 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012790 adhesive layer Substances 0.000 claims abstract description 17
- 239000003085 diluting agent Substances 0.000 claims abstract description 17
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 16
- 239000012760 heat stabilizer Substances 0.000 claims abstract description 16
- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 claims abstract description 10
- SSDBTLHMCVFQMS-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1 SSDBTLHMCVFQMS-UHFFFAOYSA-N 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 35
- 238000003756 stirring Methods 0.000 claims description 28
- 238000001035 drying Methods 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- 238000009835 boiling Methods 0.000 claims description 18
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- NADYEWVQIJRXJM-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethyl)-5-prop-2-enyl-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC=C)C(=O)N1CC1CO1 NADYEWVQIJRXJM-UHFFFAOYSA-N 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 230000001376 precipitating effect Effects 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- ZRBGKWIQVOIUEU-UHFFFAOYSA-N 2,3,5,6-tetrachloronaphthalene-1,4-dione Chemical compound ClC1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1Cl ZRBGKWIQVOIUEU-UHFFFAOYSA-N 0.000 claims description 5
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 5
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 5
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 4
- 235000013539 calcium stearate Nutrition 0.000 claims description 4
- 239000008116 calcium stearate Substances 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- 235000019359 magnesium stearate Nutrition 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 abstract description 9
- 230000032683 aging Effects 0.000 abstract description 6
- 229910052797 bismuth Inorganic materials 0.000 description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000007774 anilox coating Methods 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000000182 1,4-naphthoquinonyl group Chemical group C1(C(=CC(C2=CC=CC=C12)=O)*)=O 0.000 description 2
- 239000002042 Silver nanowire Substances 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical group [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0812—Aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/001—Conductive additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/314—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive layer and/or the carrier being conductive
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses an ultrathin conductive adhesive film which comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 60-75 parts of conductive filler, 25-45 parts of acrylic resin, 5-10 parts of diluent and 3-8 parts of isocyanate curing agent; 0.5-5 parts of a silane coupling agent; 2-6 parts of a heat stabilizer, 0.5-0.8 part of a photoinitiator, 5-8 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 1-3 parts of isocyanate ethyl acrylate, 3-6 parts of graphene-coated nano aluminum powder and 0.1-0.3 part of a catalyst. The invention also discloses a preparation method of the ultrathin conductive adhesive film. The ultrathin conductive adhesive film disclosed by the invention is ultrathin in thickness, good in adhesive property and conductivity and excellent in aging resistance.
Description
Technical Field
The invention relates to the technical field of conductive adhesive films, in particular to an ultrathin conductive adhesive film and a preparation method thereof.
Background
With the development of electronic technology, people are increasingly unable to leave electronic products in daily life and work, and pursuit of light, thin, convenient and multifunctional electronic products is also more intense. This makes the electronic components for manufacturing electronic products smaller and miniaturized, and the printed circuit board has higher and higher requirements for high density and high integration, and functionally, the electronic components need stronger and higher signal transmission. Under such a situation, a Flexible Printed Circuit (FPC) has come and its appearance has attracted much attention in the industry.
The conductive adhesive film is often used in the process of manufacturing the flexible circuit board, and the conductive adhesive film can simultaneously realize the functions of conductivity and gluing and fixing. The performance of the conductive adhesive film directly affects the service life and normal use stability of the flexible circuit board. Most of the existing conductive adhesive films take copper foils, conductive fabrics and the like as base materials or have no base materials but have thicker thickness, although the conductive adhesive films have good conductivity, the oxidation of the base materials such as the copper foils still brings some problems, bad phenomena are easy to occur due to the base materials in the die cutting process, the conductive adhesive films are heavy in quality and do not accord with the pursuit of people for lightness, thinness and convenience at present. The substrate-free conductive adhesive tape has good flexibility and bonding performance, but most of the existing conductive adhesives are epoxy resin-based conductive adhesives, the epoxy resin-based conductive adhesives have high viscosity, low heat resistance, poor chemical resistance and toughness and expensive fillers, and particularly, the traditional single metal powder or graphite conductive fillers are difficult to uniformly coat, so that the coating operation is disturbed, the product manufacturing efficiency is low, the product cannot be further improved, and the production cost is high. Other kinds of non-base material conductive adhesive films on the market also have the defects of low bonding strength, poor heat resistance and the like after hot-pressing and curing.
In order to solve the problems, the Chinese invention patent CN102993995B discloses a preparation method of a transparent conductive adhesive film, which comprises the steps of firstly, uniformly dispersing ethanol solution of silver nanowires on the surface of a transparent PET film by using a film scraping rod; and then drying at 60 ℃ for 10min to completely volatilize ethanol, finally covering a layer of oily paper on the surface of the PET film, transferring the PET film to a flat hot press, heating, pressurizing, forming a film and cooling to obtain the transparent conductive adhesive film. However, the conductive adhesive film has a high manufacturing cost due to the use of the silver nanowires, and in addition, the conductive adhesive film has a defect that the aging resistance and the adhesive strength are to be further improved.
Therefore, the need still exists in the art for an ultrathin conductive adhesive film with ultrathin thickness, good adhesive property and conductivity and excellent aging resistance and a preparation method thereof.
Disclosure of Invention
The invention mainly aims to solve the technical problems and provides an ultrathin conductive adhesive film with ultrathin thickness, good adhesive property and conductivity and excellent aging resistance and a preparation method thereof.
In order to achieve the above purpose, the present invention provides an ultrathin conductive adhesive film, which is characterized by comprising a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 60-75 parts of conductive filler, 25-45 parts of acrylic resin, 5-10 parts of diluent and 3-8 parts of isocyanate curing agent; 0.5-5 parts of a silane coupling agent; 2-6 parts of a heat stabilizer, 0.5-0.8 part of a photoinitiator, 5-8 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 1-3 parts of isocyanate ethyl acrylate, 3-6 parts of graphene-coated nano aluminum powder and 0.1-0.3 part of a catalyst.
Preferably, the catalyst is an organic bismuth catalyst DY-20.
Preferably, the source of the graphene-coated nano aluminum powder has no special requirement, and in an embodiment of the present invention, the graphene-coated nano aluminum powder is prepared by the method of embodiment 1 in chinese patent 201510319344.3.
Preferably, the preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting for 8-10 hours at 70-80 ℃, then reducing the temperature to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 3-6 times, and then removing the diethyl ether by rotary evaporation to obtain the 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
Preferably, the molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione to the amino-terminated polyurethane to the basic catalyst to the polymerization inhibitor to the high-boiling-point solvent is 1:1 (0.8-1.2) to (0.1-0.3) to (8-13).
Preferably, the source of the amino-terminated polyurethane is not particularly required, and in one embodiment of the present invention, the amino-terminated polyurethane is prepared by the method of example 1 in chinese patent application 201510152019.2.
Preferably, the polymerization inhibitor is at least one selected from tetrachloronaphthoquinone and 1, 4-naphthoquinone.
Preferably, the alkaline catalyst is one or more of sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide; the high boiling point solvent is one or more of dimethyl sulfoxide, N-dimethylformamide and N-methylpyrrolidone.
Preferably, the photoinitiator is at least one of benzoin ethyl ether, benzoin dimethyl ether and 2, 4-dihydroxy benzophenone.
Preferably, the heat stabilizer is one or more of calcium stearate, barium stearate and magnesium stearate.
Preferably, the silane coupling agent is at least one of a silane coupling agent KH550, a silane coupling agent KH560 and a silane coupling agent KH 570.
Preferably, the isocyanate curing agent is an isocyanate curing agent CX-8320.
Preferably, the diluent is one or more of methyl methacrylate, butyl methacrylate, hydroxypropyl methacrylate and triethylene glycol dimethacrylate.
Preferably, the acrylic resin is Mitsubishi acrylic resin MB-2595.
Preferably, the conductive filler is one or more of conductive silver powder, silver-coated copper powder and nickel powder; the particle size of the conductive filler is less than 10 mu m.
Preferably, the conductive silver powder is nano silver powder, and the nickel powder is selected from nickel powder with the particle size of 5 μm.
Preferably, the release film is any one of a PE release film, a PET release film, a PS isolation film, and a PMMA release film.
Another objective of the present invention is to provide a method for preparing the ultrathin adhesive film, which comprises the following steps: mixing the components according to the weight part to obtain a mixed material, adding a solvent with the mass 1-2 times of that of the mixed material, stirring for 10-20min at 1000r/min by using a dispersion machine, then stirring for 10-30min at 3500r/min by using 2500 + and then stirring for 30-90min at 3000r/min by using 1000 + and then naturally filtering and defoaming by using a filter screen, coating the mixture on a release film through a knife edge or a reticulate roller in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven.
Preferably, the ultraviolet curing condition is that the wavelength of ultraviolet light is 200-260nm, and the curing time is 20-30 min; the drying temperature of the oven is 80-90 ℃, and the drying is carried out until the weight is constant.
Preferably, the solvent is at least one of organic solvents such as ethyl acetate, toluene, butanone, and N-N dimethylformamide.
Due to the application of the technical scheme, the invention has the following beneficial effects:
(1) according to the preparation method of the ultrathin conductive adhesive film disclosed by the invention, the conductive filler with small particle size and a high-speed dispersion machine are used for uniformly dispersing the conductive filler in the resin, and the coating mode of an anilox roller or a knife edge is adopted, so that the ultrathin adhesive film is realized, and the use requirement is met.
(2) The ultrathin conductive adhesive film disclosed by the invention adopts a substrate-free structure, so that the problem caused by oxidation of the copper foil of the traditional copper foil-based conductive adhesive film is avoided.
(3) The invention discloses an ultrathin conductive adhesive film, which is prepared from the following components in parts by weight: 60-75 parts of conductive filler, 25-45 parts of acrylic resin, 5-10 parts of diluent and 3-8 parts of isocyanate curing agent; 0.5-5 parts of a silane coupling agent; 2-6 parts of a heat stabilizer, 0.5-0.8 part of a photoinitiator, 5-8 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 1-3 parts of isocyanate ethyl acrylate, 3-6 parts of graphene-coated nano aluminum powder and 0.1-0.3 part of a catalyst. The components are matched with each other and act together, so that the prepared adhesive film is ultrathin in thickness, good in adhesive property and conductivity and excellent in aging resistance; by adopting the acrylic resin-based conductive adhesive film, the problems of long curing time, high glass transition temperature, medium bonding strength and the like of the traditional epoxy resin-based conductive adhesive film are solved, the epoxy resin-based conductive adhesive film can be quickly cured, the time of a production process can be effectively reduced, the glass transition temperature is low, and the bonding strength is high.
(4) According to the ultrathin conductive adhesive film disclosed by the invention, the propenyl on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer in the conductive adhesive layer can be subjected to copolymerization curing reaction with other components containing unsaturated ethylenic bonds under the action of a photoinitiator; meanwhile, isocyanate groups on the isocyanate ethyl acrylate and the isocyanate curing agent can be subjected to a crosslinking curing reaction with amino groups on the 2, 2-bis [4- (4-aminophenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, acrylic resin and active hydrogen on the diluent, so that the components are connected together by chemical bonds to form an interpenetrating network structure, the comprehensive performance and the performance stability of the adhesive film are effectively improved, and the service life of the adhesive film is longer.
(5) According to the ultrathin conductive adhesive film disclosed by the invention, the acrylate, triazinetrione, hexafluoropropane, phenoxy and polyurethane structures are simultaneously introduced into the molecular structure of the adhesive film, and under the influence of various effects, the structures are mutually matched and act together, so that the prepared adhesive film has sufficient aging resistance and long service life. The addition of the graphene coated nano aluminum powder and the synergistic effect of the graphene coated nano aluminum powder and the conductive filler can enhance the conductivity of the adhesive film and reduce the cost.
Detailed Description
The following description is presented to disclose the invention so as to enable any person skilled in the art to practice the invention. The preferred embodiments in the following description are given by way of example only, and other obvious variations will occur to those skilled in the art.
The graphene-coated nano aluminum powder in each embodiment of the invention is prepared by the method of embodiment 1 in Chinese patent 201510319344.3; the amino-terminated polyurethane is prepared according to the method of example 1 in Chinese patent application 201510152019.2.
Example 1
The ultrathin conductive adhesive film comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 60 parts of conductive filler, 25 parts of acrylic resin, 5 parts of diluent and 3 parts of isocyanate curing agent; 0.5 part of a silane coupling agent; 2 parts of a heat stabilizer, 0.5 part of a photoinitiator, 5 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-aminophenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 1 part of isocyanate ethyl acrylate, 3 parts of graphene-coated nano aluminum powder and 0.1 part of a catalyst; the catalyst is an organic bismuth catalyst DY-20.
The preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting at 70 ℃ for 8 hours, then reducing to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 3 times, and then performing rotary evaporation to remove the diethyl ether to obtain the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
The molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst, a polymerization inhibitor and a high-boiling point solvent is 1:1:0.8:0.1: 8; the polymerization inhibitor is tetrachloronaphthoquinone; the alkaline catalyst is sodium carbonate; the high boiling point solvent is dimethyl sulfoxide.
The photoinitiator is benzoin ethyl ether; the heat stabilizer is calcium stearate; the silane coupling agent is a silane coupling agent KH 550; the isocyanate curing agent is an isocyanate curing agent CX-8320; the diluent is methyl methacrylate; the acrylic resin is a Mitsubishi acrylic resin MB-2595; the conductive filler is conductive silver powder; the conductive silver powder is nano silver powder; the release film is a PE release film.
The preparation method of the ultrathin conductive adhesive film comprises the following steps: mixing the components in parts by weight to obtain a mixed material, adding a solvent with the mass 1 time that of the mixed material, stirring for 10min at 300r/min by using a dispersion machine, then stirring for 10min at 2500r/min, then stirring for 30min at 1000r/min, naturally filtering and defoaming by using a filter screen, coating on a release film through a knife edge in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven; the ultraviolet curing condition is that the wavelength of ultraviolet light is 200nm, and the curing time is 20 min; the drying temperature of the oven is 80 ℃, and the drying is carried out until the weight is constant; the solvent is ethyl acetate.
Example 2
The ultrathin conductive adhesive film comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 63 parts of conductive filler, 30 parts of acrylic resin, 6 parts of diluent and 4 parts of isocyanate curing agent; 1.5 parts of a silane coupling agent; 3 parts of a heat stabilizer, 0.6 part of a photoinitiator, 6 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-aminophenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane 2.5 parts, 1.5 parts of isocyanate ethyl acrylate, 4 parts of graphene-coated nano aluminum powder and 0.15 part of a catalyst; the catalyst is an organic bismuth catalyst DY-20.
The preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, a basic catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting for 8.5 hours at 72 ℃, then reducing to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 4 times, and then performing rotary evaporation to remove the diethyl ether to obtain the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
The molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione to the amino-terminated polyurethane to the high-boiling-point solvent is 1:1:0.9:0.15: 9; the polymerization inhibitor is 1, 4-naphthoquinone; the alkaline catalyst is potassium carbonate; the high boiling point solvent is N, N-dimethylformamide.
The photoinitiator is benzoin dimethyl ether; the heat stabilizer is barium stearate; the silane coupling agent is a silane coupling agent KH 560; the isocyanate curing agent is an isocyanate curing agent CX-8320; the diluent is butyl methacrylate; the acrylic resin is Mitsubishi acrylic resin MB-2595; the conductive filler is silver-coated copper powder; the particle size of the conductive filler is less than 10 mu m; the release film is a PET release film.
The preparation method of the ultrathin conductive adhesive film comprises the following steps: mixing the components in parts by weight to obtain a mixed material, adding a solvent with the mass 1.2 times of the mass of the mixed material, stirring for 13min at 500r/min by using a dispersion machine, then stirring for 15min at 2700r/min, then stirring for 40min at 1500r/min, naturally filtering and defoaming by using a filter screen, coating on a release film by using an anilox roller in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven; the ultraviolet curing condition is that the wavelength of ultraviolet light is 210nm, and the curing time is 22 min; the drying temperature of the oven is 83 ℃, and the drying is carried out until the weight is constant; the solvent is toluene.
Example 3
The ultrathin conductive adhesive film comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 68 parts of conductive filler, 35 parts of acrylic resin, 7 parts of diluent and 5.5 parts of isocyanate curing agent; 3 parts of a silane coupling agent; 4 parts of a heat stabilizer, 0.65 part of a photoinitiator, 6.5 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 3 parts of 2, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 2 parts of isocyanate ethyl acrylate, 4.5 parts of graphene-coated nano aluminum powder and 0.2 part of a catalyst; the catalyst is an organic bismuth catalyst DY-20.
The preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, a basic catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting at 75 ℃ for 9 hours, then reducing to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 5 times, and then performing rotary evaporation to remove the diethyl ether to obtain the 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
The molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst, a polymerization inhibitor and a high-boiling point solvent is 1:1:1:0.2: 10; the polymerization inhibitor is 1, 4-naphthoquinone; the alkaline catalyst is sodium hydroxide; the high boiling point solvent is N-methyl pyrrolidone.
The photoinitiator is 2, 4-dihydroxy benzophenone; the heat stabilizer is magnesium stearate; the silane coupling agent is a silane coupling agent KH 570; the isocyanate curing agent is an isocyanate curing agent CX-8320; the diluent is hydroxypropyl methacrylate; the acrylic resin is a Mitsubishi acrylic resin MB-2595; the conductive filler is nickel powder with the granularity of 5 mu m; the release film is a PS isolating film.
The preparation method of the ultrathin conductive adhesive film comprises the following steps: mixing the components in parts by weight to obtain a mixed material, adding a solvent with the mass 1.5 times that of the mixed material, stirring for 15min at 700r/min by using a dispersion machine, then stirring for 20min at 3000r/min, then stirring for 60min at 2000r/min, naturally filtering and defoaming by using a filter screen, coating on a release film through a knife edge in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven; the ultraviolet curing condition is that the wavelength of ultraviolet light is 230nm, and the curing time is 25 min; the drying temperature of the oven is 85 ℃, and the drying is carried out until the weight is constant; the solvent is butanone.
Example 4
The ultrathin conductive adhesive film comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 73 parts of conductive filler, 42 parts of acrylic resin, 9 parts of diluent and 7 parts of isocyanate curing agent; 4.5 parts of a silane coupling agent; 5 parts of heat stabilizer, 0.75 part of photoinitiator, 7.5 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 3.5 parts of 2, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 2.5 parts of isocyanate ethyl acrylate, 5.5 parts of graphene-coated nano aluminum powder and 0.25 part of catalyst; the catalyst is an organic bismuth catalyst DY-20.
The preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, a basic catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting at 78 ℃ for 9.5 hours, then reducing the temperature to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 6 times, and then performing rotary evaporation to remove the diethyl ether to obtain the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
The molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst, a polymerization inhibitor and a high-boiling point solvent is 1:1:1.1:0.25: 12; the polymerization inhibitor is a mixture formed by mixing tetrachloronaphthoquinone and 1, 4-naphthoquinone according to a mass ratio of 3: 5; the alkaline catalyst is a mixture formed by mixing sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide according to the mass ratio of 1:2:2: 3; the high-boiling-point solvent is a mixture formed by mixing dimethyl sulfoxide, N-dimethylformamide and N-methylpyrrolidone according to the mass ratio of 2:1: 3.
The photoinitiator is a mixture formed by mixing benzoin ethyl ether, benzoin dimethyl ether and 2, 4-dihydroxy benzophenone according to a mass ratio of 1:3: 4; the heat stabilizer is a mixture formed by mixing calcium stearate, barium stearate and magnesium stearate in a mass ratio of 1:1: 2; the silane coupling agent is a mixture formed by mixing a silane coupling agent KH550, a silane coupling agent KH560 and a silane coupling agent KH570 according to a mass ratio of 3:1: 3; the isocyanate curing agent is an isocyanate curing agent CX-8320; the diluent is a mixture formed by mixing methyl methacrylate, butyl methacrylate, hydroxypropyl methacrylate and triethylene glycol dimethacrylate according to the mass ratio of 2:3:2: 1; the acrylic resin is a Mitsubishi acrylic resin MB-2595; the conductive filler is conductive silver powder; the conductive silver powder is nano silver powder; the release film is a PMMA release film.
The preparation method of the ultrathin conductive adhesive film comprises the following steps: mixing the components in parts by weight to obtain a mixed material, adding a solvent with the mass 1.8 times of that of the mixed material, stirring for 18min at 900r/min by using a dispersion machine, then stirring for 25min at 3300r/min, stirring for 80min at 2500r/min, naturally filtering and defoaming by using a filter screen, coating the mixture on a release film through an anilox roller in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven; the ultraviolet curing condition is that the wavelength of ultraviolet light is 250nm, and the curing time is 28 min; the drying temperature of the oven is 88 ℃, and the drying is carried out until the weight is constant; the solvent is N-N dimethylformamide.
Example 5
The ultrathin conductive adhesive film comprises a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 75 parts of conductive filler, 45 parts of acrylic resin, 10 parts of diluent and 8 parts of isocyanate curing agent; 5 parts of a silane coupling agent; 6 parts of a heat stabilizer, 0.8 part of a photoinitiator, 8 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 4 parts of 2, 2-bis [4- (4-aminophenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 3 parts of isocyanate ethyl acrylate, 6 parts of graphene-coated nano aluminum powder and 0.3 part of a catalyst; the catalyst is an organic bismuth catalyst DY-20.
The preparation method based on the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, a basic catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting at 80 ℃ for 10 hours, then reducing the temperature to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 6 times, and then performing rotary evaporation to remove the diethyl ether to obtain the 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
The molar ratio of the 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst, a polymerization inhibitor and a high-boiling point solvent is 1:1:1.2:0.3: 13; the polymerization inhibitor is tetrachloronaphthoquinone; the alkaline catalyst is potassium hydroxide; the high boiling point solvent is dimethyl sulfoxide; the photoinitiator is benzoin ethyl ether; the heat stabilizer is barium stearate; the silane coupling agent is a silane coupling agent KH 550; the isocyanate curing agent is an isocyanate curing agent CX-8320; the diluent is hydroxypropyl methacrylate; the acrylic resin is a Mitsubishi acrylic resin MB-2595; the conductive filler is nickel powder with the granularity of 5 mu m; the release film is a PE release film.
The preparation method of the ultrathin conductive adhesive film comprises the following steps: mixing the components in parts by weight to obtain a mixed material, adding a solvent with the mass 2 times that of the mixed material, stirring for 20min at 1000r/min by using a dispersion machine, then stirring for 30min at 3500r/min, then stirring for 90min at 3000r/min, naturally filtering and defoaming by using a filter screen, coating the mixture on a release film through an anilox roller in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven; the ultraviolet curing condition is that the wavelength of ultraviolet light is 260nm, and the curing time is 30 min; the drying temperature of the oven is 90 ℃, and the drying is carried out until the weight is constant; the solvent is ethyl acetate.
Comparative example 1
The invention provides an ultrathin conductive adhesive film, which is similar to the formula and the preparation method of the ultrathin conductive adhesive film in example 1, except that 2, 2-bis [4- (4-aminophenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane and graphene-coated nano aluminum powder are not added.
Comparative example 2
The invention provides an ultrathin conductive adhesive film, which is similar to the formula and the preparation method of the ultrathin conductive adhesive film in example 1, except that 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer and graphene-coated nano aluminum powder are not added.
In order to further illustrate the beneficial technical effects of the ultrathin conductive adhesive films prepared in the embodiments of the present invention, the ultrathin conductive adhesive films prepared in the embodiments 1-5 and the comparative examples 1-2 were subjected to the related performance tests, and the test results and the test methods are shown in table 1.
TABLE 1
| Item | Thickness of adhesive tape | Adhesive force | Resistance (RC) |
| Unit of | μm | gf/25mm | Ω/□ |
| Test method | GB/T7125-1999 | GB/T2792-1998 | Four-probe test method |
| Example 1 | 8 | 1792 | 11.2 |
| Example 2 | 10 | 1809 | 10.0 |
| Example 3 | 10 | 1835 | 9.0 |
| Example 4 | 12 | 1867 | 7.5 |
| Example 5 | 9 | 1848 | 6.8 |
| Comparative example 1 | 10 | 1735 | 36.5 |
| Comparative example 2 | 10 | 1703 | 38.0 |
As can be seen from table 1, the ultrathin adhesive film disclosed in the examples of the present invention has more excellent adhesion and conductivity than the comparative product, which is the result of the synergistic effect of the components.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are merely illustrative of the principles of the invention, but various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. The ultrathin conductive adhesive film is characterized by comprising a release film and a conductive adhesive layer coated on the release film, wherein the conductive adhesive layer is prepared from the following components in parts by weight: 60-75 parts of conductive filler, 25-45 parts of acrylic resin, 5-10 parts of diluent and 3-8 parts of isocyanate curing agent; 0.5-5 parts of a silane coupling agent; 2-6 parts of a heat stabilizer, 0.5-0.8 part of a photoinitiator, 5-8 parts of 1, 3-bis (ethylene oxide methyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer, 2-bis [4- (4-amino phenoxy) phenyl ] -1,1,1,3,3, 3-hexafluoropropane, 1-3 parts of isocyanate ethyl acrylate, 3-6 parts of graphene-coated nano aluminum powder and 0.1-0.3 part of a catalyst.
2. The ultrathin adhesive film of claim 1, wherein the catalyst is an organobismuth catalyst DY-20.
3. The ultrathin adhesive film of claim 1, wherein the preparation method based on 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino terminated polyurethane polymer comprises the following steps: adding 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, amino-terminated polyurethane, an alkaline catalyst and a polymerization inhibitor into a high boiling point solvent, stirring and reacting for 8-10 hours at 70-80 ℃, then reducing the temperature to room temperature, precipitating in water, washing the precipitated polymer with diethyl ether for 3-6 times, and then removing the diethyl ether by rotary evaporation to obtain the 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione/amino-terminated polyurethane polymer.
4. The ultra-thin conductive adhesive film of claim 3, wherein the molar ratio of the 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, the amino-terminated polyurethane, the alkaline catalyst, the polymerization inhibitor and the high boiling point solvent is 1:1 (0.8-1.2): 0.1-0.3: 8-13.
5. The ultrathin adhesive film of claim 3, wherein the polymerization inhibitor is at least one selected from tetrachloronaphthoquinone and 1, 4-naphthoquinone; the alkaline catalyst is one or more of sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide; the high boiling point solvent is one or more of dimethyl sulfoxide, N-dimethylformamide and N-methylpyrrolidone.
6. The ultrathin adhesive film of claim 1, wherein the photoinitiator is at least one of benzoin ethyl ether, benzoin dimethyl ether, and 2, 4-dihydroxybenzophenone; the heat stabilizer is one or more of calcium stearate, barium stearate and magnesium stearate; the silane coupling agent is at least one of a silane coupling agent KH550, a silane coupling agent KH560 and a silane coupling agent KH 570.
7. The ultra-thin conductive adhesive film of claim 1, wherein the isocyanate-based curing agent is an isocyanate curing agent CX-8320; the diluent is one or more of methyl methacrylate, butyl methacrylate, hydroxypropyl methacrylate and triethylene glycol dimethacrylate; the acrylic resin is a Mitsubishi acrylic resin MB-2595.
8. The ultrathin adhesive film of claim 1, wherein the conductive filler is one or more of conductive silver powder, silver-coated copper powder and nickel powder; the particle size of the conductive filler is less than 10 mu m; the release film is any one of a PE release film, a PET release film, a PS isolation film and a PMMA release film.
9. The method for preparing the ultrathin adhesive film of any one of claims 1 to 8, comprising the following steps: mixing the components according to the weight part to obtain a mixed material, adding a solvent with the mass 1-2 times of that of the mixed material, stirring for 10-20min at 1000r/min by using a dispersion machine, then stirring for 10-30min at 3500r/min by using 2500 + and then stirring for 30-90min at 3000r/min by using 1000 + and then naturally filtering and defoaming by using a filter screen, coating the mixture on a release film through a knife edge or a reticulate roller in a workshop, and preparing the ultrathin conductive adhesive film after ultraviolet curing and drying in an oven.
10. The method for preparing the ultra-thin conductive adhesive film as claimed in claim 9, wherein the ultraviolet curing condition is that the wavelength of the ultraviolet light is 200 and 260nm, and the curing time is 20-30 min; the drying temperature of the oven is 80-90 ℃, and the drying is carried out until the weight is constant; the solvent is at least one of organic solvents such as ethyl acetate, toluene, butanone and N-N dimethylformamide.
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| CN116285830A (en) * | 2023-03-13 | 2023-06-23 | 湖南联兴光电科技有限公司 | Thermosetting adhesive, adhesive tape and preparation method thereof |
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